Jack pulled up to Bobby's early on the morning that Dean's deal was due. He was equally relieved and dismayed that the Impala wasn't in the driveway. It was close to 3:00 in the morning and even Rumsfeld, Bobby's old dog, didn't raise the alarm in the silence. Jack was weary to the bone. Grabbing his duffel, he got out of the car Bobby had loaned him and closed the door as quietly as possible. Moving towards the door, Jack stopped at the sound of footsteps behind him. Turning swiftly, he peered into the darkness trying to see what had made the sound.

The moon cast a shadow as the figure of a petite woman stepped out from behind a heap of junk. Jack's breath caught as adrenaline surged into his blood and slowly Jack began to back up towards the door.

"Wait!" the figured called quietly. "Wait! I can help!"

Jack stopped but didn't move towards the figure. "Who are you?"

"I'm a friend of Sam's . . . or I was . . .before. My name is Ruby. And you're Jack, right?"

"How do you know who I am?" Jack said suspiciously. He knew his brothers tried to keep him off the radar the first year they had known about each other.

"I was actually with Sam when he found you and Dean in that cabin. Unfortunately, I wasn't able to stay and keep everything from going to hell but . . ." Ruby slowly moved towards Jack with both hands out in a non-threatening gesture. As she drew closer, Jack was surprised by the pretty, heart-shaped face under the curly black hair. Why would Sam involve a 110 lb. girl in hunting? Jack thought to himself.

Ruby stopped two feet in front of Jack. "In fact, in a way, I know you better than I know Sam. I'm the one that actually got you to the hospital. . . ."

Jack frowned. He had never really had a chance to ask Sam how he had gotten both him and Dean from the cabin to the Impala all by himself but sometimes, he dreamed about it. He dreamed that he was walking and talking and helping Sam carry Dean down the hill but it wasn't really him at all. He always woke up from those dreams in a sweat, afraid that he was losing his mind, that he was scitzophrenic like his mother's first husband had been.

Ruby took a step closer and Jack was caught by how small she was, how sweet her smile was, how blue her eyes. He started to smile back when suddently the blue turned to black.

"Oh Shit!" Jack yelped, startled. Jack's body automatically started moving backwards but he lost his balance, landing on his back. Ruby laughed delightedly as Jack started to crab walk back, trying to get away. Two quick strides forward and Ruby squatted down to sit on Jack's chest.

"Come on Jackie boy, there's no need to be rude here. We're all on the same side."

"The hell we are," Jack stuttered trying to get out from under the demon. She was surprising heavy for such a petite thing.

"Oh come on now, you would have died up there if I hadn't taken control of your body and gotten down the hill," Ruby smiled again, reaching down to push Jack's hair out of his eyes. "If you think about it, I have been closer to you than any other woman has been – or ever will be . . . . we've shared a body."

Jack's eyes widened in realization. "Possessed! I was possessed! That's why I keep having those dreams. Wait . . ." Jack said as a second thought hit him. "Sam let you possess me? What the hell?"

Ruby's smiled widened into a grin. "I told you I was a friend. I mean Sammy wouldn't have trusted me with his baby brother's body if I had been the enemy, now would he?" Ruby stood up and offered a hand out to Jack. Jack took it warily and pulled himself to his feet. Ruby continued more seriously, "Of course that little trick took me out of the fight at the worst time possible." Ruby moved back and leaned up against the car with her arms crossed. "It took me a good day to find another meat suit I could live with. By that time, Sam had already called on O'ray and made the deal. If I had been there, I could have told him that wasn't Lilith in the hospital. Talk about bad timing. . . ."

"but you're a demon . . ." Jack said, trying to make sure he understood everything Ruby had told him.

"Yes, yes, I'm a demon. Please tell me you're aren't a bigot like Dean," Ruby huffed in frustration.

"No. I mean Yeah, I guess. Aren't you the bad guy? Aren't you happy Sam has gone all dark side?"

"Don't make the same mistake Dean does. Nothing in life is black and white. There are many various shades of gray. I am not the bad guy. I want Sam Winchester back the way he was – exactly the way he was. I am not happy about his metamorphisis and I want to help, if I can."

"Uhh Okay," Jack said unplussed. He really had no idea what to make of the offer of help. Everything he had learned, everything his brother and Bobby said hadn't prepared him for Ruby.

Lights flashed over Ruby's face and disappeared. Jack turned to see headlights coming down the lane. As he turned back, Ruby had moved back into the shadows. "Uh ohh! Big brother's home. I'm going to take off. He really hates me – no matter how many times I've saved his ass. . ."

"Wait!" Jack said stepping forward. "Do you know how we can beat this deal? Get Sam back?"

"Not yet, but I'll think of something. I'll be in touch" Ruby said as she faded into the darkness.

Turning, Jack watched as the Impala came to a stop beside him. Dean immediately jumped out, 9 mm in hand. Glancing around, he said, "What?"

Jack looked at him confused, wondering if Dean had seen Ruby. "What, what?"

Dean narrowed his eyes at his youngest brother, wondering if he was hiding something. "What are you doing out here in the middle of the night staring at the wreck of a '68 Nova?"

"Oh," Jack said relieved. "I just got back into town. I thought I heard something but it was just a stray cat. You scared it away when you pulled up." Jack didn't know why he thought it was important to keep Ruby's visit a secret from Dean. He just did.

"Oh," Dean answered. Clicking the safety back on, he threw the pistol into his duffel. "Just got back from where?"

"Home – I had to go home. How did it go?"

"It didn't," Dean muttered. "But I think I might have an idea."

"Yeah? Me too." Jack turned towards the house but the rush of the adrenline had left him weak and shaky. Dean reached out to steady his youngest brother.

"Well, it can wait until I've had a shower and at least 6 hours of sleep," Dean said climbing the porch steps as he took in Jack's weary face and tired eyes. "We'll talk about it over breakfast."

"But," Jack started.

Dean held up his hand stopping Jack in mid sentence. "Shower, Sleep, Food, Talk – in that order." Dean quietly let himself into the front door. Jack paused and looked once more around the junk yard before following.